Sodium Cyanide → 1-(Diphenylmethyl)azetidine-3-carbonitrile

HRID 1900601Notes

Reaction equation

HRID 1900601 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16](OS(C)(=O)=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:23]#[N:24].[Na+]>CN(C)C=O.O>[CH:1]([N:14]1[CH2:17][CH:16]([C:23]#[N:24])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 27792901-(Diphenylmethyl)azetidine-3-carbonitrileYield 51.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 50 g (0.157 mol) of 1-benzhydryl-3-mesyloxyazetidine (J. Org. Chem. 1972, 37, 3953-3955) and 23.5 g (0.479 mol) of sodium cyanide in 340 ml of dimethylformamide and 43 ml of water is heated to 60° C. for 5 hours. The reaction mixture is left at ambient temperature overnight and is then poured into 2000 ml of water/ice. The solid product is recovered by filtration and is purified by being suspended in 800 ml of water and being filtered. The product thus obtained is dried and crystallized from isopropyl ether to obtain 20 g of 1-benzhydryl-3-azetidinecarbonitrile. M.p. 142°-146° C.

Workup

  1. filtrationThe solid product is recovered by filtration
  2. customis purified
  3. filtrationbeing filtered
  4. customThe product thus obtained
  5. customis dried
  6. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-f018046e90d043e4a274a520c5c87562
Source dataset
uspto-grants-1996_11
Patent number
US05576320

Reaction notes

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